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Haloalkanes And Haloarenes

Question
CBSEENCH12011268
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Which one is most reactive towards SN1 reaction?

  • C6H5CH(C6H5)Br

  • C6H5CH(CH3)Br

  • C6H5C(CH3)(C6H5)Br

  • C6H5CH2Br

Solution

C.

C6H5C(CH3)(C6H5)Br

SN1 reaction involves the formation of carbocation intermediate. More the stability of carbocation more is the reactivity of alkyl/aryl halides towards SN1 reaction. 
The intermediate carbocations formed by given halides as:
 
straight a right parenthesis space straight C subscript 6 straight H subscript 5 CH left parenthesis straight C subscript 6 straight H subscript 5 right parenthesis Br space rightwards arrow space left parenthesis straight C subscript 6 straight H subscript 5 right parenthesis subscript 2 straight C to the power of plus straight H space space plus space Br to the power of minus straight b right parenthesis space straight C subscript 6 straight H subscript 5 CH left parenthesis CH subscript 3 right parenthesis Br space rightwards arrow space straight C subscript 6 straight H subscript 5 straight C to the power of plus straight H left parenthesis CH subscript 3 right parenthesis space plus space Br to the power of minus straight c right parenthesis space straight C subscript 6 straight H subscript 5 straight C left parenthesis CH subscript 3 right parenthesis left parenthesis straight C subscript 6 straight H subscript 5 right parenthesis Br space rightwards arrow space left parenthesis straight C subscript 6 straight H subscript 5 straight C to the power of plus left parenthesis CH subscript 3 right parenthesis space plus space Br to the power of minus straight d right parenthesis space straight C subscript 6 straight H subscript 5 CH subscript 2 Br space rightwards arrow space straight C subscript 6 straight H subscript 5 straight C to the power of plus straight H subscript 2 space plus space Br to the power of minus The space order space of space stability space of space these space carbocations space is space as left parenthesis straight C subscript 6 straight H subscript 5 straight C to the power of plus left parenthesis CH subscript 3 right parenthesis space greater than left parenthesis straight C subscript 6 straight H subscript 5 right parenthesis subscript 2 straight C to the power of plus straight H space greater than straight C subscript 6 straight H subscript 5 straight C to the power of plus straight H left parenthesis CH subscript 3 right parenthesis space greater than space straight C subscript 6 straight H subscript 5 straight C to the power of plus straight H subscript 2
Thus, C6H5C(CH3)(C6H5)Br is most reactive towards SN1 reaction.

Some More Questions From Haloalkanes and Haloarenes Chapter

Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields:

i)Three isomeric monochlorides.

Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields:
Four isomeric monochlorides.

Draw the structures of major monohalo products in each of the following reactions:

Draw the structures of major monohalo products in each of the following reactions:

Draw the structures of major monohalo products in each of the following reactions:

Draw the structures of major monohalo products in each of the following reactions:

Draw the structures of major monohalo products in each of the following reactions:

Arrange each set of compounds in order of increasing boiling points:
Bromomethane, Bromoform, Chloro-methane, Dibromomethane.

Arrange each set of compounds in order of increasing boiling points:
1-chloropropane, Isopropyl chloride, 1-chlorobutane.

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